


Little Milker

by BottomDean67



Category: Supernatural
Genre: Anal Pump, Anal Sex, Body Modification, Bondage, Bottom Dean Winchester/Top Sam Winchester, Butt Plugs, Cock Cages, Collars, Consensual, Forced Orgasm, Gags, M/M, Male Lactation, Nipple Clamps, Nipple Play, Overstimulation, Rough Oral Sex, hole spanking, milker!Dean, penis gag
Language: English
Status: Completed
Published: 2020-09-04
Updated: 2020-09-04
Packaged: 2021-03-06 21:28:49
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 1,623
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26285710
Author URL: https://archiveofourown.org/users/BottomDean67/pseuds/BottomDean67
Summary: Sam's newest milker, Dean, is ready to be milked for the first time, a highly specialized blend Sam can sell for a high dollar. Watching his big brother get milked and fucked has it's perks too.A/N: Dean consensually signed up to be a milker for a big payday and because he loves getting used.
Relationships: Dean Winchester/Sam Winchester
Comments: 3
Kudos: 197





	1. Chapter 1

“How’s our newest milker doing?” asked Sam as he walked into the preparation room. “Is he finally ready?”

“His hormone levels look good. Thanks to the new mix, his milk is going to sell for a fortune,” said the caretaker that was grabbing a file. “I love when we do the specialty blends.”

“I know we haven’t done a mixture of this magnitude before,” said Sam, taking the folder that was handed to him. “I want him monitored closely this first month. Orgasms make the milk better but with the adjustments made, he’s going to be doing it often.  _ Very _ often. I doubt after today he’ll ever come anything but dry again.”

“We’ll be very careful with our milker. He’s going to be spending a lot of time being milked and cumming. It won’t take long for him to adjust.”

Sam smiled as he watched his newest milker crawl on hands and knees into his very own private milking room. Sam wasn’t going to tell him that his waking hours, and quiet a few sleeping ones, would be spent here from now on.

The milker was led by the leash attached to his collar up onto the milking stand. He looked a bit out of it, probably from the feed, put up no resistance as he was strapped down, a special bench with an open middle so his massively full breasts would hang straight down. His head was bent downwards and a pad was secured behind him so he had a perfect view of his own breasts and caged cock. A penis gag was in his mouth for the cow to suckle on and Sam was pleased to see the cow doing just that. The cock cage was quickly removed, the milker’s penis staying flacid. 

Sam squatted down and inspected the milkers nipples. They were a deep red, pulsing almost with the need to be sucked and milked. 

“Let’s hook him up. We want the small drip suction on the nipples. I want every drop that comes out of those beautiful tits to have been pulled out of just the nipple alone. It’ll be a slower feed but we’ll be able to charge more.”

“What about his cock? Best fit?”

“This is going to be our top of the line exclusive product for years to come. I expect we put in top of the line effort.”

“Yes sir.”

Sam got out of the way as they attached the suction pumps to the milker’s nipples, Dean said the name on it’s collar. A larger one slid over his cock and they did a light pump of air through the hoses to get a perfect fit. The milker moaned and Sam smiled when he got a nod from his crew.

“Let’s get some milk boys.”

Dean let out the biggest moan of his life when the suction came on. His rock hard nipples felt like they had burst open the flood gates. They tingled, were swollen and puffy and red and it was as if he’d already gone a few rounds of having his poor buds tortured.

He knew what he signed up for. What he’d given away. 

But damn was he ready to be a milker and the fact he had no choice now made him nearly cum right then and there. The suction on his cock steadily increased as did on his nipples until it looked as though the tubes were trying to tear them away from his body. They were weighted, he could feel that but damn, did it feel  _ good _ . 

His first orgasm hit him like a freight train, cum spilling down into the tube connected to his cock. He swore someone was laughing but the earplugs prevented him from hearing a sound. The only thing he was there for was to get milked and watch himself get milked. He groaned as he saw the first droplets of white form on his buds and fall into the tube. It turned into a steady stream quickly but it was slow and his breasts still felt painfully full.

Four orgasms in ten minutes later he was coming dry, the sensitivity on his cock almost too much. His nipples were producing milk and flowing freely, Dean jerking when he felt someone remove his butt plug and shove a fat cock inside. Whoever it was did it fast and dirty, shooting cum inside of him and sending Dean into an instant orgasm.

“Oh damn. The instant orgasm to cum finally got worked out?” asked Sam to his caretaker that was pulling up his pants. 

“Oh yeah. Don’t get too greedy on me, Sam. We can’t pump him full of it all the time. His little heart couldn’t take orgasming on end like that.”

“True. Could have uses in other markets, like sex slaves. It could revamp the training industry,” said Sam.

“Always the entrepreneur, aren’t ya. Can’t you ever just enjoy a good milker getting fucked and drained?”

“Oh course. This one is handsome too. How long will he be able to produce for?”

“Might only get a year out of him cause of our modifications. I know it ain’t ideal.”

“I’ll take him as my sex slave afterwards. His ability to produce will be gone but his nipples will still be so sensitive he couldn’t even wear a shirt without orgasming. No, I’m not letting this one out of my sight.”

“His milking contract is only for the duration in which he’s able to produce. Then he’s a free man again.”

“We’ll see about that.”


	2. Little Slave

**Summary for the Chapter:**

> Sam makes Dean an offer after his milking contract is up to become his own personal sex slave...

**Nine Months Later**

“That’s it?” asked Sam as he spotted his prized milker in the recovery bay. “Nine months?”

“How much money did you make? Nine months was a lot and it’s gonna age so well and make us even more,” said the caretaker. Sam pursed his lips and the caretaker crossed his arms. “He’s a free man, boss. Touch him now and you’re gonna be paying him off not to sue.”

“I understand. I’ll watch him for the evening. It’s no trouble.”

**Two Days Later**

“Dean,” said Sam. Dean popped his head up from where he was waiting at the bus station down by the end of the entrance to the milking facility. “Running off so soon? Surprised you can wear a shirt.”

“Feels tingly,” said Dean, groaning as he stood up to hide the moan that happened as his shirt moved. “Thanks. That was intense but good intense.”

“Well...you are a whore. Might as well get paid to do it,” said Sam. “What you gonna buy? Fancy house?”

“Found dad’s old impala online. Was gonna buy it back. I offered double price to get a hold on it. I’m picking it up tomorrow.”

“I would have bought it for you. Why didn’t you just ask?” said Sam. Dean shrugged and moved purposefully this time, biting his bottom lip. “Cause you’re a whore.”

“You know it,” said Dean with a wink. “I don’t need a ride. I’m good.”

“I was thinking...if you enjoyed that...maybe you’d enjoy being my sex slave.”

“I like getting my ass pounded as much as the next guy but I ain’t giving up my freedom,” said Dean.

“Not that kind of sex slave. My personal sex slave. One where I own you purely because you want me to. It’s just between us. You have every right and freedom as you do now. If you break a rule, it’s only my rules, no legal consequence. Besides, I can fuck you up in ways you haven’t even dreamed of.”

“As long as I still get to drive that car, sign me the fuck up.”

**One Month Later**

“Sam,” breathed out Dean. He cried out on the next stroke, the tassel feature on the machine still spanking his hole and get a bit of his balls. Weights were attached to the nipple clamps that hung down towards the ground, Dean’s cock in a cage as he was whipped again. The collar on his neck had no tags now but he knew exactly who he belonged to. “Sam!”

“Either take your hole spanking or I add more weight, whore.”

“Yes sir,” said Dean. Sam smiled and let the machine go a few more minutes before he turned it off. Dean sagged in relief but Sam was right there, putting a pump over Dean’s hole. He squeezed down on the plunger and Dean made a strange grunt. 

Sam pumped it up quickly until Dean’s hole was red, fat and puffy. Dean whined but Sam left it on for ten minutes, the hole nice and plump when he removed it.

“What do you say, whore?”

“Thank you for punishing me,” said Dean.

“And?”

“And the only person allowed to play with my hole is you sir, not even me.”

“Very good.”

Sam undid the clamps and rolled Dean off the bench and onto the bed, straddling his face quickly.

“Deep throat me slut.” Sam shoved his cock in Dean’s mouth and choked him on it, Dean swallowing all around him. Sam smiled when he felt Dean gagging and grabbed Dean’s head to hold him there. “Get ready for it.”

Dean went wide eyed when Sam came, Dean bucking off the bed and grabbing the sheets as he experienced the feel of an orgasm without the satisfaction thanks to the cock cage. Dean swallowed and panted, Sam moving aside and gently playing with Dean’s nipples while he came down.

“What was that like?” asked Sam. “Still as intense?”

Dean stared at him and got a mischievous look in his eye.

“Why do I feel like you’re going to get in trouble tomorrow?” asked Sam.

“Tomorrow? I think I need another punishment Sammy. Might I suggest some wax play?”


End file.
